Arsenoarylglycollic acids.



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essaeztons no rnnnwnnxn vomu. MEISTERLUCIUS & Bnumne, .ornooHsr-otuammamgsnnarnnv, A. oon-ronarron or GERMANY.

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I Specification or Letters mat.

Application filed may 17, 1909.

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Serial No. 496,654.

To all whom it may concern:

Be it known that we, PAUL EHRLIGH, M. D., professor of medicine, and ERNST -Scnivrrrz, Ph. D., chemist, citizens of the namely arsenoarylglycollic acids, which are valuable as remedlesin infectious diseases,

can be obtained by treating arylglycolarsinic acidswith energetic reducing agents. The reaction involved derivatives.

The arylglycolarsinic acids which are to be reduced may be obtained from the oxyarylarsinic acids bycombining them with chloracetic acid, for instance as follows 240 grams ofso'dium para-oxyph'enylarsinate, dissolved in 480 grams of water, are mixed with a solution of 188 grams of chloracetic acid in 300 grams of water and with 400 grams of caustic soda lye of .per cent.

I strength. 'ThlS mixture is boiled for three hourson .a refluxap aratus; whencool it is means of concentrated hydrochloric aci while well cooling. The phenylglycolarsinic acid then separates and may be recrystallized from water or glacial acetic acid. It crystallizes in the form of small crystals; it sinters when heated to over 150 (land decomposes; it is soluble in methyLalcohol and ethyl-alcohol, almost insoluble in ether and benzene; when trtiated with alkalies it forms readilysoluble sa ts.

The process for producing the new arseno compounds may be illustrated by the following example: 800 grams of anhydrous corresponds to the aqua sodium hydrosulfite and 400 grams of magnesium chlorid are dissolved in 4000 0. cm. of water and mixed with200 grams of 10- normal caustic soda lye. To the solution, which has been filtered from'the magnesium hydroxid, 160 grams of disodium salt of the paraphenylglycolarsinic acid are added and the mixture is heated for about one hour to 45 while stirring well. The precipitate thus formed is filtered 0E and washed with wateryby re-dissolving it in the form of its sodium salt the new compound arsenophenylglycollic acid can be obtained in a ure state. The sodium salt is yellow, read 11y soluble in water, difficultl'y soluble in alcohol. by means of acetic acid as ayellow voluminous precipitate. The acid afid itssalts re- The free acid is isolated from it duce a cold ammoniacalsilver solution. In i an analogous manner other arylglycolarsinic acids, for instance orthoand Ineta-tolylglycolarsinic acids, can be converted into the correspondin arsenoarylglycollic acids, very similar to t e above described arsenophenylgl collic acid.-

The t erapeutic arseno compounds consists in destroying trypanosomesfbacterim, they are capable of curing even such animals as have been.infected with .trypanosomes of a very great resistance.

The said new compounds may be administered by injecting a solution-of 5 to 10 per cent. strength intoeth essubcutaneous con- Adm'ifiistrati'on per 0s to the present ex-. perience, it is best to a minister doses of 0.5

junctive tissue. is excluded. Accord'm grams, which are eventually repeated. v.

Having now described our invention, what we claim is 2- v i 1. As new products, the arsenoarylglycollic acids thecconstitution of which corresponds to the formula:

COOHCILO aryl As- .As aryl'OCH COOH,

being yellow powders iiiseluble in water and alcohol, forming yellow alkali salts, readily efliciency of the new collie acid, the constitution of which corresponds to the formula:

I ASG6H4OCH2QOOH, being a yellow powder insoluble in water and elcohol, forming yellow alkali salts,

readily soluble in water, diflicultly soluble in alcohol, and the solution of which reduces a cold ammoniacal silver solution.

In testimony whereof, we aifix our signa- 15 tures in presence of two witnesses.

PAUL EHBLIOH. ERNST SCHMITZ. 

